I live in Waterbury Ct area and I have traveled many times out to Pittsburgh Pa.
I will say that 84 thru Waterbury can be hit or miss because of the major construction project in Waterbury. You will be about 4 hours or so to this area when leaving Eastham if you do the Mass Pike (90) to Sturbridge (84). If you plan right hopefully the traffic back up would be light. It will be backed up from about 4pm to 7 pm in Waterbury. When I go south I skip NYC I go from Waterbury RT 8 south to Bridgeport catch 95 South to exit 21 (287) in New York State first exit I think and go about 10 miles and over the Tappan Zee Bridge (no toll going south) then out on 287 in NJ and down to 78 which will take you right to Hershey. You can also do 95 from Mass. thru Rhode Isl. down the coast of CT to exit 21.
